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Chapter 16: Q71P (page 795)

Rank the following compounds from most reactive to least reactive toward nucleophilic addition:

Short Answer

Expert verified

Most reactive least reactive

Order of reaction

Step by step solution

01

Step-by-Step Solution Step 1: Nucleophilic addition

The presence of the electron-withdrawing group increases the reactivity towards the addition while the presence of the electron-donating group decreases the reactivity of the compound towards nucleophilic addition. Benzaldehyde does not favor nucleophilic addition reaction due to resonance stabilization. The polarity of the carbonyl group is in benzaldehyde which is reduced due to the resonance making it less reactive in nucleophilic addition reactions.

02

More reactive to least reactive

Among the following compounds, para nitro benzaldehyde is more reactive towards nucleophilic addition reaction due to the presence of EWG followed by benzaldehyde and anisaldehyde. The least reactive one is isopropyl benzaldehyde due to the presence of EDG.

The order of reaction from most reactive to least reactive is as follows:

Most reactive least reactive

Order of reaction

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Most popular questions from this chapter

When a cyclic ketone reacts with diazomethane, the next larger cyclic ketone is formed. This is called a ring-expansion reaction. Draw a mechanism for the following ring-expansion reaction.

What is the product of the reaction of an ester with excess acetylide ion followed by the addition of pyridinium chloride?

Question: Fill in the boxes with the appropriate reagents:

Using cyclohexanone as the starting material, describe how each of the following compounds can be synthesized.

a.

b.

c.

d.

e.

f.

g.

h.

(show two methods)

i.

(show two methods)

The pKa of protonated acetone is about -7.5, and the pKa of protonated hydroxylamine is 6.0.

a. In a reaction with hydroxylamine at pH 4.5 (Figure 16.2), what fraction of acetone is present in its acidic, protonated form? (Hint: See Section 2.10.)

b. In a reaction with hydroxylamine at pH 1.5, what fraction of acetone is present in its acidic, protonated form?

c. In a reaction with acetone at pH 1.5 (Figure 16.2), what fraction of hydroxylamine is present in its reactive basic form?
See all solutions

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